Dan Blakeslee answers the phone with a ghoulish cackle, in full character. Most of the year he’s a troubadour, playing bluesy urban folk in music clubs and occasionally busking, in a subway station or elsewhere. At last summer’s Newport Folk Festival, his pop-up set in front of the gate managed to steal a little thunder from onstage performers at the sold-out event.

October, however, belongs to Blakeslee’s haunted alter ego, Doctor Gasp. Singing songs like “She, Vampire Tamer,” “RAWR!” and “Teeth of Candycorn” while wearing a Day of the Dead skull mask, Doctor Gasp and The Eeks aim to drain every drop of blood from All-Hallows-Eve.

His month-long Misshapen Jack-O-Lantern Tour roams the region with a goofy mix of scary and silly music. The journey always culminates with a Seacoast show. This year’s performance at Portsmouth’s Press Room will feature two more acts and is a continuation of the city’s annual parade.

“Soggy Po’ Boys will march in and start playing downstairs, and afterwards play with me upstairs; then Truffle plays,” Blakeslee said. “It will be an action-packed evening.”

The tradition began in 2002.

“I played at the Press Room two nights before Halloween and I decided I wanted to write my own Halloween song,” Blakeslee said. “It was terrible, and I played it. Someone in the audience shouted, ‘I want to put that on vinyl!’ It came out the next year, and I’ve been doing it ever since.”

True to its title, the tour often veers off-course. The Maine-born singer/guitarists will stop to play in a cornfield, graveyard or abandoned house if the mood strikes. Blakeslee seeks out offbeat venues as well; he’d just appeared at a VFW hall in Sleepy Hollow, New York — yes, the same town made famous by Washington Irving.

“I ended up getting lost once — I was trying to,” said Blakeslee of how he landed the gig. “I was like, oh my god, forget where I was supposed to go. I want to hang out here!”

Blakeslee learned to love Halloween at an early age.

“My dad was always the type of guy to put loudspeakers in the window and creepy decorations, so I had that growing up; it was super inspiring,” adding that he read classic horror — Dracula, Frankenstein — and watched scary cartoons. “Disney’s Headless Horseman, that’s a big one for me.”

His band has made a pair of studio albums, Vampire Fish in 2003 and last year’s Vampire Fish For Two. The record covers both feature distinctive pen-and-ink work from Blakeslee. He’s an in-demand artist who’s designed beer cans for The Alchemist’s Heady Topper IPA and Newburyport Brewing Company.

After the Boston Marathon terrorist attack, his folk art drawing of two hands transforming the Zakim Bridge into a heart went viral on Facebook; ultimately, the image was used to raise thousands for victims.

“I was so affected by the bombings that I just walked around all night in the rain. … I got home and I just had to get it out of me,” said Blakeslee, who lives in Somerville. “Making it was art therapy; I never thought about selling it at all.”

Blakeslee attended art school in Maryland before taking up music. He committed at the urging of his boss at Barnacle Billy’s in Ogunquit, Maine, a part-time job.

“I’d been working for seven seasons, going on my eighth,” he said. “When I went to apply for the summer, the owner said, ‘You know what? You’re not supposed to be working here; you’re supposed to be out making music.”

He offered a deal: “Book as many shows as you possibly can and the days you have off you can work here.”

“It was really incredible,” said Blakeslee. “He gave me such a push until I got going. He helped me get my first guitar that I actually started playing out with. … I’m really indebted to him.”